Hydrochloric Acid → HCID 71743116, compound

HRID 2039761Notes

Reaction equation

HRID 2039761 reaction equation
N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl[C:23]1[C:28]([NH:29][C:30](=[O:41])[C:31]2[CH:36]=[C:35]([CH3:37])[C:34]([O:38][CH3:39])=[C:33]([CH3:40])[CH:32]=2)=[CH:27][CH:26]=[C:25]([Cl:42])[N:24]=1>O1CCCC1.[Cu]I>[Cl:42][C:25]1[N:24]=[C:23]2[O:41][C:30]([C:31]3[CH:36]=[C:35]([CH3:37])[C:34]([O:38][CH3:39])=[C:33]([CH3:40])[CH:32]=3)=[N:29][C:28]2=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 86675960HCID 86675960, compound

Product 1

HCID 71743116HCID 71743116, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
140 °C

Procedure

In a microwaveable vessel, 1.03 g of N-(2,6-dichloropyridin-3-yl)-4-methoxy-3,5-dimethylbenzamide were dissolved in 15 ml of dry tetrahydrofuran, and 30 mg of copper(I) iodide, 57 mg of 1,10-phenanthroline and 1.54 g of cesium carbonate were added. In a microwave sunthesizer, the reaction mixture was then heated at 140° C. for 2 h. For work-up, the mixture was added to 10 ml of a 0.5 M aqueous hydrochloric acid solution. The mixture was extracted twice with ethyl acetate. The collected organic phases were combined and the solvent was removed under reduced pressure. This gave 0.88 g (98%) of the product, which was reacted further without any further purification.

Workup

  1. extractionThe mixture was extracted twice with ethyl acetate
  2. customthe solvent was removed under reduced pressure
  3. customThis gave 0.88 g (98%) of the product, which was reacted further without any further purification

Sources & evidence

ORD record
ord-d026dacb5f244ee68a2ac913d357a14e
Source dataset
uspto-grants-2013_11
Patent number
US08580816B2

Reaction notes

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